Joseph and I sat down with someone we really admire a few weeks ago, Jena of ChiCity Fashion. Not only did she give us valuable advice about the real world…but now we know what restaurants to check out in Chicago. Success.

ALEX: So what did you study in school?

JENA: Marketing. I just knew that I wanted to do some kind of fashion marketing or apparel merchandising. I never wanted to do design because I knew that I’m creative, but I’ve never been good at art or sewing or anything like that. But I wanted to pick my school based on the school, not a specific program. I didn’t want to go to a specialty school I guess. I don’t even know why I went to Miami of Ohio, it’s so not me. Marketing was just the closest thing I could find that fit my interest in fashion.

ALEX: Did you start your blog in college, or after you graduated?

JENA: Yes, I started it at the very end of first semester of my senior year. I was just bored and totally over the night life at school. I actually started on Twitter. I made a Twitter to keep up with celebrities and found that I really enjoyed the fashion presence on Twitter, like the magazines and designers. I didn’t tweet anything for a few months and then I finally got up the courage to tweet style tips and random things I would find. Then I got a little bit of a following and people would tweet me and ask me if I had a blog, but I didn’t know a lot about it at the time. I knew I definitely didn’t just want to do a personal style blog like “oh come take pictures of me.” At Miami that just wasn’t a thing. Someone had suggested WordPress to me, so I checked it out and made one and I didn’t tell anyone about it because for the first three months I was so embarrassed about it. I didn’t even tell my boyfriend and we’ve been together for almost five years. Then, I got invited to a show at fashion week so I was like “Is this real?” I thought it was a joke, but I was like “Let’s just try it,” so that’s when I had to tell people. So it was cool, but one of my friends met me and came with me so it was really fun.

ALEX: That’s a crazy experience! I can only imagine.

JENA: Yeah I still didn’t feel comfortable telling people about it unless they asked me about it, up until maybe around when I started working at eDrop-Off. They were the first ones who really embraced it and wanted to do stuff with me, and it made me feel a little bit more comfortable about it. And now it’s my job!

ALEX: Can’t be embarrassed about it anymore!

JENA: So that…long story short…more long then short..is how that happened.

ALEX: How was the transition from working in fashion, to just being a blogger? Was it difficult?

JENA: Well lately I’ve just been having a lot of meetings, where people I’ve either worked with before but haven’t met yet just want to meet me in person, or companies want to present me with a new idea or some people kind of just want my opinion. There’s lots of different reasons to have meetings, believe me. I was kind of nervous about the transition at first like “Oh am I going to be sitting at home all the time?” But I’m not at all, which is great. I also have more time to kind of make my blog better. I used a free template for my site until I decided to make ChiCityFashion my full time job. Now I’m working on a mobile site so I’m just always looking for ways to improve. I’ve been doing a lot of research lately.

ALEX: I love your layout already, it’s super easy to navigate which is a nice change from other sites. Where do you see it going from here?

JENA: I’m really bad at answering those questions. I kind of just wing everything. I don’t just want to be a blogger forever. It’s great for right now, but I don’t think it’s going to be a sustainable career forever, so I’m still trying to figure out what my next move will be. I like being on my own, my parents are entrepreneurs .I’ve always wanted to own my own business, I’m just trying to figure out exactly what I want to do. I also really love food, so sometimes I’m just like I love fashion, but there’s a lot of crap that comes with it and I don’t like dealing with that, but I’m sure that’s how the food industry is too. Lately I’ve just been really interested in it.

ALEX: Food is always good. Do you think you’ll go into styling?

JENA: When I graduated college I really wanted to be a stylist, but that was at the time that everyone wanted to be a stylist, or “was” a stylist. Once something gets saturated I just move on. I like the idea of it, but I like to do it on a personal level. Anything from “I need help getting ready for an event,” to “I just need a whole new wardrobe.” I would much rather do that then go be responsible for a $100,000 worth of clothes and then pull all this stuff, and in the end, only one look is used. I love the idea of it, but I’m not passionate to do that part. Does that make sense?

ALEX: Yeah, that sounds really overwhelming and kind of scary.

JENA: The thing that I did with FORD Chicago was perfect because I directed it and assistant styled.

ALEX: What does that mean?

JENA: I came up with the concept, I chose the models, the locations, and all that stuff. My friends Michael is a stylist, so he styled and I went with him on the pulls, but he actually did the pulling. So then when it came down to it, he dressed the models and I just helped out. It was the perfect situation. I remember when he was pulling things he showed me these pants and I was like “those are so ugly!” But he came back and was like “We have to use them!” and I was like “Really??” They were like…these snake print and yellow wide leg pants…and this green jacket…and it sounds crazy, but it looks so cool! It’s stuff like that, where I would never have thought to put that together. I’m more realistic on what I would put together. When it comes to photography, it doesn’t really matter.

ALEX: You have to have a different eye. It’s so different. For people looking to get into fashion, or really anything I guess, what advice would you give them?

JENA: it’s so cliché…but don’t give up. If you truly want to do something, put all you have into it, and it will happen. There is no reason that it shouldn’t if you give it your all. I mean, I still don’t even know what I’m doing! People email me that question all the time. I feel bad, because everything I did was kind of by accident, so I can’t really give advice on how it happened. I know someone who is very passionate about being in fashion somehow, but his parents don’t agree with that. There are a lot of parents out there who want their kid to be a lawyer or whatever. He just doesn’t care though and he’s such a hustler and does whatever he can to make it work. I know that whatever he decides to do, he’s going to be great at it, because of his work ethic. Also, do your research. A lot of people think they like fashion, just because they like shopping, and that’s how I was when I was younger. But once I did my research, I was genuinely interested in it. I feel like a lot of people just say that they work in fashion or start a blog and expect to become a blogger super star, and it doesn’t work that way. I just write what I want and some people like it. You have to be authentic with it. I don’t try to hide anything.

ALEX: You can tell when someone’s writing just to be popular. We see a lot of that lately. It’s kinda weird. There was a blog that popped up a few months ago that would literally copy my posts.

JENA: That’s so stupid! Did you end it?

JOSEPH: Yeah. We also had an issue with the DePaulia asking to use our street style photos for their newspaper and we were immediately like…no. They wound up not even running the story.

ALEX: Have you ever had an issue with people copying your site? How did you deal with it?

JENA: There’s smaller instances, but more with my personal style. The only big issue I’ve had with my site, and I don’t even understand how this happened, but it was called “Fashion201.com” and they were copying everything. The same day, for about two weeks, they copied my photos, tags…everything. It was still in first person…so weird. So I found this person and I stalked them.

JOSEPH: Did they have a following?

JENA: No. Nothing. They had no social media sites. At first, I thought it was a virus. I emailed them at first, but they didn’t do anything, so I had my attorney send a letter and they took it down right away. That was the only direct instance. With blogging in general, there’s going to be a lot of times when people copy you, and it won’t be as direct as that. But I know, and it just makes me be even more creative and come up with new things.

ALEX:If you could look back and give yourself advice just starting out in your career, or in college, what would you say?

JENA: I guess it would be, know what you’re worth. I underestimated myself, especially in the beginning. I got screwed over so many times, and it’s hard for me to be assertive. At the end of the day, it’s really just me and what I write, and it’s hard to put a price on that. But, I’ve had people promise me things or I’m supposed to get paid for things, and then they don’t pay me. So, it’s really just about being more assertive and knowing what you’re worth. And that’s with any job. It’s so easy to get taken advantage of. When I got out of college, I had so many unpaid internships, so that too. Don’t do it for too long. Some people do it for over a year, and then they get pissed. But at the same time, you can quit whenever you want. So don’t let people take advantage of you either.

JOSEPH: [Gesturing to the wall of designer items] Do any of these have stories?

JENA: They all have stories.

JOSEPH: Can we hear some?

JENA: Those are probably my favorite story, the black and white wedges. Proenza Schouler is my favorite designer and that was the collection that truly made me fall in love with them. It was Spring 2010. I’m very motivated when it comes to getting things. If I have my eye on something, I have to get it. I was stalking the shoes, and it was before they had a store so it was super hard to track things down. I fell in love with a different version of these that were on the runway. They wound up not making the runway version into production. I was on the Out-Net one day and saw those at 70% off and they only had my size so I got them and I love them.

ALEX: I’m obsessed with the PS1 medium in the “crowd” print.

JENA: The crowd print! I was at the store, and what they’ve been doing, which I like, is the materials they’ve been using lately is amazing quality. Their finale dress was a crowd print perforated dress, which I’m sure is just astronomical, but they also do a different version of the print on just a silk dress. I’ll show you. Most of the things in here are my favorite things. And all of my handbags.

ALEX: What’s the story behind your custom PS1?

JENA: I am so careful with it. It was after the earthquake in Japan, and the designers in the CFDA all donated something. It was super close to my birthday, and I wound up getting it for like half the price of what it was, and I was going to New York anyway. So I went to their office and I got to meet with Jack and Lazaro, and I was dying. I got to shop the sample sale by myself. It was so cool. It was awesome because they let me use any material I wanted except alligator or croc, so I chose python. It’s a custom color. My initials are on a plaque inside. It’s crazy.

Alex: How long did it take them to get it to you?

JENA: I made it in July, and I don’t think I got it until December. They had to stop their whole production to do it. They had never made a custom PS1 before.

JENA: I actually really like black and white. It’s technically a trend, but I don’t know if I would consider it a trend. I would say peplum is more of a trend. I love it because it’s still neutral to wear other colors and I can add pops of accessories and bright lipstick. It’s shaking things up from wearing all black, and there’s a million ways you can do it. It never gets old.

ALEX: Alright, so I have a few final questions. Where can we find you shopping in Chicago?

JENA: I prefer Blake and Ikram for higher end shopping. I personally prefer Ikram because everything you see in the store is so beautiful…and their cafe is so good. Sofia Boutique has been my go to store since forever. They use to be in an office building on Clark and Division and I use to go there on my breaks when I would come home from college. I love the stuff that they buy. I also really like Edith Hart.All the places on Damen Ave. are pretty good.

ALEX: And because you love food, I have to ask what your favorite restaurants are right now.

JENA: I hate when people ask me that because it’s so hard to choose! I told you about Eleven City Diner. It makes me so happy. It’s very casual, on 11th and Wabash. It’s super good comfort food. Spacca Napoli out in Ravenswood is my favorite pizza place. The guy who owns it is certified to make Neapolitan style pizza. They make their own cheese, and it’s so simple but the ingredients are incredible. The one I always get literally just has mozzarella, arugula, and basil, but it’s the best pizza. To go with friends, pretty much anything on Randolph St. Like Nellcote, and Au Cheval. Floriole on Webster is also a big go to of mine. I’ve also been to Antique Taco a whole bunch of times, and that’s probably my favorite Mexican food in Chicago. For sushi, I love Arami. It’s hard to find really good sushi here.

ALEX:Any last words for us?

JENA: I had to learn how to negotiate and figure out what I’m worth and just price out certain things and it’s hard. Just try to get everything in writing. I got screwed over so many times because I didn’t have it in writing. I’ve had to learn who I want to work with, and who I don’t want to work with and how I want to do things. Think about the things you want to take on and if it’s worth it. In the beginning, I took on everything. As annoying as it was, I’ve learned so much doing this.

ALEX: People don’t realize that being a blogger is journalism and being an entrepreneur.

JENA: One problem that i’ve noticed, is that a lot of companies don’t know how to work with bloggers. I’m always approached by a PR company, it’s rarely directly with the brand. The bigger companies already know exactly what they want. A lot of people don’t understand how a blogger functions and I get that because it’s very new and unique. Everything in blogging and social media for a business is so new and people just don’t know what to do with it.